NPASS Compound

Structure

CID44732 OpenBabel06191715382D 22 23 0 0 1 0 0 0 0 0999 V2000 -3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 2 3 1 0 0 0 0 3 14 1 0 0 0 0 4 6 2 0 0 0 0 4 12 1 0 0 0 0 5 7 2 0 0 0 0 5 13 1 0 0 0 0 6 18 1 0 0 0 0 7 17 1 0 0 0 0 8 12 1 0 0 0 0 8 15 1 0 0 0 0 9 12 2 0 0 0 0 9 16 1 0 0 0 0 10 13 2 0 0 0 0 10 14 1 0 0 0 0 11 15 1 0 0 0 0 11 19 1 0 0 0 0 13 16 1 0 0 0 0 14 17 2 0 0 0 0 15 20 1 0 0 0 0 16 18 2 0 0 0 0 17 21 1 0 0 0 0 18 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	300.14
Volume:	319.477
LogP:	3.089
LogD:	2.678
LogS:	-3.378
# Rotatable Bonds:	6
TPSA:	80.92
# H-Bond Aceptor:	4
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.618
Synthetic Accessibility Score:	2.879
Fsp3:	0.222
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.617
MDCK Permeability:	8.232380423578434e-06
Pgp-inhibitor:	0.024
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.048
20% Bioavailability (F20%):	0.997
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.065
Plasma Protein Binding (PPB):	98.1927261352539%
Volume Distribution (VD):	0.505
Pgp-substrate:	1.9621825218200684%

ADMET: Metabolism

CYP1A2-inhibitor:	0.821
CYP1A2-substrate:	0.128
CYP2C19-inhibitor:	0.33
CYP2C19-substrate:	0.066
CYP2C9-inhibitor:	0.322
CYP2C9-substrate:	0.762
CYP2D6-inhibitor:	0.782
CYP2D6-substrate:	0.884
CYP3A4-inhibitor:	0.439
CYP3A4-substrate:	0.344

ADMET: Excretion

Clearance (CL):	13.469
Half-life (T1/2):	0.853

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.043
Drug-inuced Liver Injury (DILI):	0.038
AMES Toxicity:	0.43
Rat Oral Acute Toxicity:	0.216
Maximum Recommended Daily Dose:	0.339
Skin Sensitization:	0.92
Carcinogencity:	0.326
Eye Corrosion:	0.003
Eye Irritation:	0.294
Respiratory Toxicity:	0.051

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC44732

Natural Product ID:	NPC44732
*Common Name:**	Magnolignan
IUPAC Name:	3-[4-hydroxy-3-(4-hydroxy-3-prop-2-enylphenyl)phenyl]propane-1,2-diol
Synonyms:	Magnolignan
Standard InCHIKey:	LHJCLTLPXXKFTJ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H20O4/c1-2-3-14-10-13(5-7-17(14)21)16-9-12(4-6-18(16)22)8-15(20)11-19/h2,4-7,9-10,15,19-22H,1,3,8,11H2
SMILES:	C=CCc1cc(ccc1O)c1cc(ccc1O)CC(CO)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL399697
PubChem CID:	5319203
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000041] Biphenyls and derivatives

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1659613]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[17918910]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	Stems; Barks	n.a.	n.a.	PMID[19086868]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	bark	n.a.	PMID[23823874]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28485933]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	6

Activity Type	# Activity
Cell Line	5
CELL-LINE	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	5.0	ug.mL-1	PMID[519173]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	5.0	ug.mL-1	PMID[519173]
NPT111	Cell Line	K562	Homo sapiens	IC50	>	5.0	ug.mL-1	PMID[519173]
NPT2341	Cell Line	NCI-H1975	Homo sapiens	IC50	>	40000.0	nM	PMID[519174]
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	>	40000.0	nM	PMID[519174]
NPT22158	CELL-LINE	HCC827	Homo sapiens	IC50	>	40000.0	nM	PMID[519174]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC44732 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	284
0.1-0.2	1404
0.2-0.3	3965
0.3-0.4	12425
0.4-0.5	7059
0.5-0.6	8347
0.6-0.7	6937
0.7-0.8	2024
0.8-0.85	178
0.85-0.9	56
0.9-0.95	11
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9903	High Similarity	NPC308689
0.9623	High Similarity	NPC473137
0.9623	High Similarity	NPC12656
0.9612	High Similarity	NPC262365
0.9314	High Similarity	NPC168829
0.9223	High Similarity	NPC288411
0.9135	High Similarity	NPC138942
0.9029	High Similarity	NPC40258
0.9029	High Similarity	NPC91461
0.9029	High Similarity	NPC7686
0.902	High Similarity	NPC78119
0.902	High Similarity	NPC132078
0.902	High Similarity	NPC216468
0.902	High Similarity	NPC51333
0.8932	High Similarity	NPC213730
0.8899	High Similarity	NPC228425
0.8899	High Similarity	NPC228988
0.8889	High Similarity	NPC174096
0.8889	High Similarity	NPC79793
0.8889	High Similarity	NPC120982
0.8889	High Similarity	NPC147634
0.8889	High Similarity	NPC226401
0.885	High Similarity	NPC182240
0.8835	High Similarity	NPC128723
0.8829	High Similarity	NPC474486
0.8807	High Similarity	NPC179002
0.8807	High Similarity	NPC257430
0.8807	High Similarity	NPC187583
0.8796	High Similarity	NPC62258
0.8796	High Similarity	NPC55617
0.8772	High Similarity	NPC223451
0.8772	High Similarity	NPC473136
0.875	High Similarity	NPC294741
0.8739	High Similarity	NPC120280
0.8718	High Similarity	NPC231767
0.8716	High Similarity	NPC296683
0.8716	High Similarity	NPC475018
0.8692	High Similarity	NPC54765
0.8692	High Similarity	NPC271274
0.8679	High Similarity	NPC323810
0.8649	High Similarity	NPC141003
0.8649	High Similarity	NPC35344
0.8644	High Similarity	NPC127975
0.8641	High Similarity	NPC82664
0.8641	High Similarity	NPC292730
0.8641	High Similarity	NPC132271
0.8641	High Similarity	NPC216520
0.8636	High Similarity	NPC95716
0.8627	High Similarity	NPC151715
0.8627	High Similarity	NPC128062
0.8621	High Similarity	NPC31936
0.8598	High Similarity	NPC233396
0.8598	High Similarity	NPC154899
0.8571	High Similarity	NPC225506
0.8559	High Similarity	NPC46940
0.8559	High Similarity	NPC286222
0.8558	High Similarity	NPC77492
0.8544	High Similarity	NPC26244
0.8532	High Similarity	NPC95344
0.8529	High Similarity	NPC271440
0.8522	High Similarity	NPC151197
0.8519	High Similarity	NPC135464
0.8519	High Similarity	NPC92623
0.8509	High Similarity	NPC477136
0.8496	Intermediate Similarity	NPC147179
0.8491	Intermediate Similarity	NPC471578
0.8491	Intermediate Similarity	NPC101025
0.8476	Intermediate Similarity	NPC122005
0.8476	Intermediate Similarity	NPC92730
0.8476	Intermediate Similarity	NPC252821
0.8462	Intermediate Similarity	NPC473388
0.8455	Intermediate Similarity	NPC254833
0.8455	Intermediate Similarity	NPC228343
0.8455	Intermediate Similarity	NPC58865
0.8448	Intermediate Similarity	NPC475245
0.8431	Intermediate Similarity	NPC45040
0.8426	Intermediate Similarity	NPC219286
0.8426	Intermediate Similarity	NPC99557
0.8421	Intermediate Similarity	NPC38893
0.8421	Intermediate Similarity	NPC219112
0.8421	Intermediate Similarity	NPC477137
0.8421	Intermediate Similarity	NPC308828
0.8421	Intermediate Similarity	NPC308311
0.8407	Intermediate Similarity	NPC268160
0.8393	Intermediate Similarity	NPC43525
0.8381	Intermediate Similarity	NPC225464
0.8378	Intermediate Similarity	NPC132720
0.8378	Intermediate Similarity	NPC63345
0.8365	Intermediate Similarity	NPC274678
0.8365	Intermediate Similarity	NPC8392
0.8364	Intermediate Similarity	NPC233835
0.8364	Intermediate Similarity	NPC61885
0.8364	Intermediate Similarity	NPC63698
0.835	Intermediate Similarity	NPC325292
0.835	Intermediate Similarity	NPC138117
0.8348	Intermediate Similarity	NPC299180
0.8333	Intermediate Similarity	NPC300017
0.8333	Intermediate Similarity	NPC471511
0.8333	Intermediate Similarity	NPC192948
0.8333	Intermediate Similarity	NPC35797
0.8319	Intermediate Similarity	NPC715
0.8319	Intermediate Similarity	NPC471485
0.8318	Intermediate Similarity	NPC51015
0.8305	Intermediate Similarity	NPC251259
0.8304	Intermediate Similarity	NPC4493
0.8304	Intermediate Similarity	NPC151537
0.8304	Intermediate Similarity	NPC476632
0.8304	Intermediate Similarity	NPC165770
0.8304	Intermediate Similarity	NPC225679
0.8304	Intermediate Similarity	NPC177576
0.8293	Intermediate Similarity	NPC143483
0.8288	Intermediate Similarity	NPC473524
0.8288	Intermediate Similarity	NPC314187
0.8276	Intermediate Similarity	NPC471671
0.8276	Intermediate Similarity	NPC469609
0.8273	Intermediate Similarity	NPC151477
0.8269	Intermediate Similarity	NPC76938
0.8261	Intermediate Similarity	NPC154511
0.8261	Intermediate Similarity	NPC257540
0.8261	Intermediate Similarity	NPC473556
0.8261	Intermediate Similarity	NPC469663
0.8261	Intermediate Similarity	NPC247858
0.8261	Intermediate Similarity	NPC301651
0.8261	Intermediate Similarity	NPC137496
0.8261	Intermediate Similarity	NPC92
0.8261	Intermediate Similarity	NPC261973
0.8261	Intermediate Similarity	NPC474358
0.8261	Intermediate Similarity	NPC474387
0.8257	Intermediate Similarity	NPC474839
0.8257	Intermediate Similarity	NPC239291
0.8252	Intermediate Similarity	NPC204210
0.8246	Intermediate Similarity	NPC107240
0.8246	Intermediate Similarity	NPC195922
0.8235	Intermediate Similarity	NPC471794
0.823	Intermediate Similarity	NPC290353
0.823	Intermediate Similarity	NPC153795
0.823	Intermediate Similarity	NPC42911
0.822	Intermediate Similarity	NPC131868
0.8214	Intermediate Similarity	NPC13482
0.8214	Intermediate Similarity	NPC252544
0.8214	Intermediate Similarity	NPC321252
0.8208	Intermediate Similarity	NPC474073
0.8208	Intermediate Similarity	NPC156313
0.8208	Intermediate Similarity	NPC32674
0.8205	Intermediate Similarity	NPC470215
0.8205	Intermediate Similarity	NPC109371
0.8205	Intermediate Similarity	NPC470214
0.8205	Intermediate Similarity	NPC469644
0.8198	Intermediate Similarity	NPC11554
0.819	Intermediate Similarity	NPC304510
0.819	Intermediate Similarity	NPC145023
0.819	Intermediate Similarity	NPC476266
0.819	Intermediate Similarity	NPC313650
0.819	Intermediate Similarity	NPC277588
0.819	Intermediate Similarity	NPC172219
0.819	Intermediate Similarity	NPC175799
0.819	Intermediate Similarity	NPC144682
0.819	Intermediate Similarity	NPC200988
0.819	Intermediate Similarity	NPC32714
0.819	Intermediate Similarity	NPC610
0.8182	Intermediate Similarity	NPC248904
0.8165	Intermediate Similarity	NPC238696
0.8165	Intermediate Similarity	NPC119860
0.8165	Intermediate Similarity	NPC475225
0.8158	Intermediate Similarity	NPC123175
0.8158	Intermediate Similarity	NPC176730
0.8158	Intermediate Similarity	NPC322239
0.8158	Intermediate Similarity	NPC117846
0.8158	Intermediate Similarity	NPC261343
0.8151	Intermediate Similarity	NPC237667
0.8151	Intermediate Similarity	NPC475166
0.8148	Intermediate Similarity	NPC110764
0.8148	Intermediate Similarity	NPC12221
0.8137	Intermediate Similarity	NPC104216
0.8136	Intermediate Similarity	NPC265454
0.8136	Intermediate Similarity	NPC472071
0.8136	Intermediate Similarity	NPC34634
0.813	Intermediate Similarity	NPC472968
0.813	Intermediate Similarity	NPC471064
0.8125	Intermediate Similarity	NPC474272
0.8125	Intermediate Similarity	NPC265211
0.8125	Intermediate Similarity	NPC306045
0.812	Intermediate Similarity	NPC86198
0.812	Intermediate Similarity	NPC154030
0.8095	Intermediate Similarity	NPC27323
0.8095	Intermediate Similarity	NPC316301
0.8095	Intermediate Similarity	NPC289769
0.8095	Intermediate Similarity	NPC152415
0.8091	Intermediate Similarity	NPC117115
0.8087	Intermediate Similarity	NPC285350
0.8083	Intermediate Similarity	NPC150026
0.8083	Intermediate Similarity	NPC71094
0.8077	Intermediate Similarity	NPC304541
0.8073	Intermediate Similarity	NPC168393
0.8073	Intermediate Similarity	NPC235762
0.8073	Intermediate Similarity	NPC233827
0.8073	Intermediate Similarity	NPC108497
0.8073	Intermediate Similarity	NPC471228
0.807	Intermediate Similarity	NPC302371
0.807	Intermediate Similarity	NPC471179

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC44732 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	270
0.1-0.2	901
0.2-0.3	1355
0.3-0.4	2846
0.4-0.5	1957
0.5-0.6	1164
0.6-0.7	561
0.7-0.8	85
0.8-0.85	8
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8654	High Similarity	NPD3020	Approved
0.8544	High Similarity	NPD2860	Approved
0.8544	High Similarity	NPD2859	Approved
0.8455	Intermediate Similarity	NPD3022	Approved
0.8455	Intermediate Similarity	NPD3021	Approved
0.8447	Intermediate Similarity	NPD2934	Approved
0.8447	Intermediate Similarity	NPD2933	Approved
0.819	Intermediate Similarity	NPD1809	Phase 2
0.8173	Intermediate Similarity	NPD845	Approved
0.8108	Intermediate Similarity	NPD2342	Discontinued
0.8095	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.807	Intermediate Similarity	NPD7635	Approved
0.8	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD3092	Approved
0.7982	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7966	Intermediate Similarity	NPD3091	Approved
0.7886	Intermediate Similarity	NPD3094	Phase 2
0.7869	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.785	Intermediate Similarity	NPD844	Approved
0.7818	Intermediate Similarity	NPD940	Approved
0.7818	Intermediate Similarity	NPD846	Approved
0.7778	Intermediate Similarity	NPD288	Approved
0.7748	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7734	Intermediate Similarity	NPD4060	Phase 1
0.7727	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7686	Intermediate Similarity	NPD4589	Approved
0.7686	Intermediate Similarity	NPD3095	Discontinued
0.7667	Intermediate Similarity	NPD5304	Approved
0.7667	Intermediate Similarity	NPD5303	Approved
0.7656	Intermediate Similarity	NPD6407	Approved
0.7656	Intermediate Similarity	NPD6405	Approved
0.7578	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7573	Intermediate Similarity	NPD111	Approved
0.7568	Intermediate Similarity	NPD3028	Approved
0.7568	Intermediate Similarity	NPD1242	Phase 1
0.7565	Intermediate Similarity	NPD2684	Approved
0.7563	Intermediate Similarity	NPD7157	Approved
0.7542	Intermediate Similarity	NPD2229	Approved
0.7542	Intermediate Similarity	NPD2228	Approved
0.7542	Intermediate Similarity	NPD2234	Approved
0.7541	Intermediate Similarity	NPD2286	Discontinued
0.7541	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3027	Phase 3
0.75	Intermediate Similarity	NPD4750	Phase 3
0.75	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.748	Intermediate Similarity	NPD2861	Phase 2
0.7458	Intermediate Similarity	NPD7843	Approved
0.7422	Intermediate Similarity	NPD4908	Phase 1
0.7419	Intermediate Similarity	NPD1610	Phase 2
0.7395	Intermediate Similarity	NPD5283	Phase 1
0.7381	Intermediate Similarity	NPD8651	Approved
0.7353	Intermediate Similarity	NPD3400	Discontinued
0.735	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD497	Approved
0.7328	Intermediate Similarity	NPD290	Approved
0.7328	Intermediate Similarity	NPD1613	Approved
0.7328	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD4103	Phase 2
0.7323	Intermediate Similarity	NPD1164	Approved
0.7323	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD4093	Discontinued
0.7302	Intermediate Similarity	NPD4659	Approved
0.728	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.728	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6355	Discontinued
0.7258	Intermediate Similarity	NPD6516	Phase 2
0.7258	Intermediate Similarity	NPD4059	Approved
0.7258	Intermediate Similarity	NPD5846	Approved
0.7258	Intermediate Similarity	NPD2932	Approved
0.7258	Intermediate Similarity	NPD3019	Approved
0.7258	Intermediate Similarity	NPD4626	Approved
0.725	Intermediate Similarity	NPD496	Approved
0.725	Intermediate Similarity	NPD495	Approved
0.725	Intermediate Similarity	NPD498	Approved
0.7241	Intermediate Similarity	NPD968	Approved
0.7236	Intermediate Similarity	NPD7330	Discontinued
0.7236	Intermediate Similarity	NPD1548	Phase 1
0.7227	Intermediate Similarity	NPD228	Approved
0.7222	Intermediate Similarity	NPD2561	Approved
0.7222	Intermediate Similarity	NPD2562	Approved
0.7209	Intermediate Similarity	NPD5736	Approved
0.7203	Intermediate Similarity	NPD1792	Phase 2
0.7197	Intermediate Similarity	NPD3062	Approved
0.7197	Intermediate Similarity	NPD3620	Phase 2
0.7197	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD3061	Approved
0.7197	Intermediate Similarity	NPD3059	Approved
0.719	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD1131	Approved
0.7188	Intermediate Similarity	NPD1135	Approved
0.7188	Intermediate Similarity	NPD1129	Approved
0.7188	Intermediate Similarity	NPD1134	Approved
0.7188	Intermediate Similarity	NPD1133	Approved
0.7176	Intermediate Similarity	NPD6798	Discontinued
0.7164	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD3552	Approved
0.7164	Intermediate Similarity	NPD3554	Approved
0.7164	Intermediate Similarity	NPD3553	Approved
0.7164	Intermediate Similarity	NPD4538	Approved
0.7164	Intermediate Similarity	NPD3555	Approved
0.7164	Intermediate Similarity	NPD4536	Approved
0.7132	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7131	Intermediate Similarity	NPD6671	Approved
0.712	Intermediate Similarity	NPD9381	Approved
0.712	Intermediate Similarity	NPD9384	Approved
0.7111	Intermediate Similarity	NPD5960	Phase 3
0.7111	Intermediate Similarity	NPD5588	Approved
0.7099	Intermediate Similarity	NPD4625	Phase 3
0.7094	Intermediate Similarity	NPD1444	Approved
0.7094	Intermediate Similarity	NPD1445	Approved
0.709	Intermediate Similarity	NPD5314	Approved
0.7068	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD5451	Approved
0.7054	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD4235	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD5691	Approved
0.704	Intermediate Similarity	NPD1651	Approved
0.704	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD6583	Phase 3
0.7031	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD1669	Approved
0.7031	Intermediate Similarity	NPD6582	Phase 2
0.7025	Intermediate Similarity	NPD9377	Approved
0.7025	Intermediate Similarity	NPD9379	Approved
0.7023	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD856	Approved
0.7016	Intermediate Similarity	NPD16	Approved
0.7015	Intermediate Similarity	NPD5735	Approved
0.7008	Intermediate Similarity	NPD1091	Approved
0.7008	Intermediate Similarity	NPD1201	Approved
0.7	Intermediate Similarity	NPD3691	Phase 2
0.7	Intermediate Similarity	NPD3690	Phase 2
0.7	Intermediate Similarity	NPD6584	Phase 3
0.6992	Remote Similarity	NPD6387	Discontinued
0.6992	Remote Similarity	NPD6663	Approved
0.6984	Remote Similarity	NPD2668	Approved
0.6984	Remote Similarity	NPD5126	Approved
0.6984	Remote Similarity	NPD1751	Approved
0.6984	Remote Similarity	NPD2667	Approved
0.6984	Remote Similarity	NPD5125	Phase 3
0.6977	Remote Similarity	NPD5310	Approved
0.6977	Remote Similarity	NPD5311	Approved
0.6977	Remote Similarity	NPD1283	Approved
0.6961	Remote Similarity	NPD9294	Approved
0.696	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD2424	Discontinued
0.695	Remote Similarity	NPD7041	Phase 2
0.695	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD4208	Discontinued
0.694	Remote Similarity	NPD3597	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD5408	Approved
0.6934	Remote Similarity	NPD5405	Approved
0.6934	Remote Similarity	NPD5404	Approved
0.6934	Remote Similarity	NPD5406	Approved
0.6934	Remote Similarity	NPD2935	Discontinued
0.693	Remote Similarity	NPD9273	Approved
0.6929	Remote Similarity	NPD3143	Discontinued
0.6929	Remote Similarity	NPD3847	Discontinued
0.6929	Remote Similarity	NPD3421	Phase 3
0.6923	Remote Similarity	NPD3055	Approved
0.6923	Remote Similarity	NPD9610	Approved
0.6923	Remote Similarity	NPD3053	Approved
0.6923	Remote Similarity	NPD9608	Approved
0.6923	Remote Similarity	NPD1470	Approved
0.6917	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD9618	Approved
0.6911	Remote Similarity	NPD9614	Approved
0.6911	Remote Similarity	NPD2629	Approved
0.6901	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD9622	Approved
0.6897	Remote Similarity	NPD4380	Phase 2
0.6885	Remote Similarity	NPD5535	Approved
0.6885	Remote Similarity	NPD1138	Approved
0.6884	Remote Similarity	NPD5762	Approved
0.6884	Remote Similarity	NPD5763	Approved
0.6884	Remote Similarity	NPD7266	Discontinued
0.688	Remote Similarity	NPD317	Approved
0.688	Remote Similarity	NPD318	Approved
0.687	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD4248	Discontinued
0.6861	Remote Similarity	NPD7743	Approved
0.6861	Remote Similarity	NPD7742	Approved
0.686	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD4535	Phase 3
0.6857	Remote Similarity	NPD4628	Phase 3
0.6855	Remote Similarity	NPD709	Approved
0.6842	Remote Similarity	NPD7095	Approved
0.6838	Remote Similarity	NPD2568	Approved
0.6838	Remote Similarity	NPD9500	Approved
0.6838	Remote Similarity	NPD4097	Suspended
0.6831	Remote Similarity	NPD2420	Approved
0.6831	Remote Similarity	NPD2421	Approved
0.6825	Remote Similarity	NPD7741	Discontinued
0.6822	Remote Similarity	NPD3070	Discontinued
0.6822	Remote Similarity	NPD2235	Phase 2
0.6822	Remote Similarity	NPD2233	Approved
0.6822	Remote Similarity	NPD2230	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data